I kept looking out the window of the van as I was transported to prison. The judge gave me 7 years, I’m thinking I might be out in 5 for good behaviour. A lot of reporters took pictures…to be expected I guess. After all I’m the first guy in history to be sent to Changi Women’s Prison. Due to an admin error, I was assigned an F gender from birth even though I’m a complete natural male. They couldn’t overturn the ruling, so they made a countermeasure instead. I was given two jabs. One to ensure my sperm would not get anyone pregnant, and a second that reduced my strength to lesser than an average female adult. They thought I’d start raping women once I got inside. If only they knew…
We finally arrive at last. The guards led me to a secured area, uncuffed me and ordered me to strip naked. Piece by piece, I removed my shirt, pants, and lastly my briefs. It’s really uncomfortable being naked and stared at by a bunch of female guards. Seeing that this is a special case, the highest ranked ASP Leow decides to inspect me herself, and turned me around.
The stern and nasty ASP Leow
I can hear her putting gloves on as the sound of rubber snaps against her wrist. She inspects my hair, ears, rubs her hands around my body…then reached for my private parts. She squeezed different portions of my cock lightly, then my balls. I winced a little, closing up my thighs, and got scolded.
“I softly touch only you react so big for what? Keep your legs open!” she reprimanded.
“Sorry madam!” I quickly apologise, and kept my legs apart.
She quickly slid her hand underneath my balls to my asscheeks, and spread wide to inspect my asshole. Then I could feel her cold fingers sink a few centimetres into my anus. I winced again and let out a shriek.
“Shut up! Don’t move!” she roared at me again. I try to keep calm as she had her way with my ass for about two minutes, probing and poking. Finally, she was done.
“2049, go shower.”
That’s my name from now on, as I enter the shower to clean myself under the watchful eyes of the guards. I could hear them murmur amongst themselves.
“The skin so smooth. I think this boy virgin!”
“You see the cock, dunno when erect how big. Really want to spank that ass!”
I forgot to mention. I’ve been given 24 strokes as well. Though it’s far from as painful as the ones that the men prison gets. The cane they decided on is practically the ones you can buy from mama shops. It won’t scar, but they were intent to teach me a lesson.
Once done, I put on my orange prison attire as I am led down the hallway to my cell. It’s just like in the movies…everyone howling and whistling at me like I’m a piece of fresh meat. I tried to look away but every corner was a woman wanting to get a piece of me. There are a few familiar faces, such as DJs on drug charges, and those involved in the Country Harvest Church scandal.
I am finally led to my cell, the door shuts and locks. I see my cellmate for my stay here, lying in bed reading a book, on the lower of the two level bunk bed. She turns to look at me.
“Hey new cellmate. I’m Stefanie, nice to meet you.”
I heave a sigh of relief. Stefanie is very pleasant looking and polite. Tall, too.
“Hi Stefanie. I’m Joe. Happy to meet you too. Just wished it wasn’t in here haha.” I try making light of my predicament.
“So I’ve heard, that your gender is F even though you’re fully male from birth, correct?”
“Yeah, weird case eh? I never changed it and got to avoid NS. I guess this is karma.”
“Don’t worry, you’ll be fine here. I’ll take care of you.”
“Thanks! I could really use a friend in here.”
I left her to do her reading as I climbed on top to check out my bed. To my horror, the mattress is torn with springs protruding up and is impossible to sleep on! I went to the door to try and signal a guard to complain, but they all ignored me.
“Hey what’s wrong?” Stef asked.
“My bed, the mattress…it’s torn, I can’t possibly sleep on it!”
“Ah…the guards don’t bother with changing stuff in here. Hey, if you don’t mind squeezing you can share mine.”
“Uh…is that really fine with you?”
“Sure! It gets cold at night, we could warm each other.”
She stood up and invited me to crawl in. Man, she even wants me to take the spot on the inside. I feel very uneasy but the court trial had left me sleepless for a few nights and I really need a nap right now.
“Ok sis, thanks. I really need a quick nap.” I said.
I crawl in and lie down, face away from her toward the wall. I can smell the light scent of her body and hair on the bed and pillow…it’s pretty fragrant actually. I close my eyes and start to doze off.
Until…I suddenly feel a hand rubbing against my crotch.
Man, I should have known that all the women here are sex starved, I just didn’t imagine nice Stefanie would do such a thing. I’m too tired so I just ignored it. Then it gets worse. She starts sliding her hand inside my pants to reach for my cock and balls directly. I continue to try sleeping and make some attempts to push her hand away, but my reduced strength meant I was no match.
She then starts kissing my neck and whispered in my ear. “Want zehzeh to make you happy?”
I couldn’t take it anymore.
“Look, Stef, I’m really not in the mood right now. And we could get in trouble for this. How about you just leave me alone and let me nap, I’m really damn tired.”
To my shock, she starts choking my neck with her other hand and squeezed my balls tight. I try to shout for help but no sound came out.
“You fucking cheebye. Chiobu offer herself to you you give me attitude?”
“Please…stop…no…”
I nearly pass out until she finally let go. I’m no longer able to make a defense of any kind. She pulls down my pants and starts sucking on my penis, forcing me to get aroused, while she toyed with my body with her hands.
“Don’t suck…don’t suck…” was all I could say as I protested. She paid no mind and continued sucking me off. I just wish she could get it over quickly.
She does stop after what felt like ten minutes, only to take off her pants and mounted herself on me. She aimed my cock at her vagina, then sat down on it, hard, while using her hands to hold mine down to the side. I try resisting again to no avail as she tongue kissed me while riding me. I could feel her pussy tightening around my cock like it was choking it as she rode faster and faster, and it was starting to hurt. She looks at me dead in the eye.
“Kena rape by chiobu shiok or not? I confirm make you shoot!”
It wasn’t until she said the r word that I realized what this really was. Female on male rape…I never would’ve thought it would be this traumatizing. I’ve lost my body, but I’m determined not to lose my mind as I tried hard not to cum.
But it’s no use. Her cunt was so tight, it was only a matter of time. My cock didn’t feel like it belonged to me…it was her toy, and I was going to cum when she wants me to, whether I want to or not. I start moaning as she moved her left hand from holding me down to covering my mouth.
“Mmmmmhmm!! Mhhmmm!!!” was all I could say.
“Cum for zehzeh you little bitch boy!”
I experience the first unwilling orgasm of my life as ropes of semen fired out from my penis, deep inside her cunt. I wanted to stop, but it keeps ejaculating as she kept riding. I came for a crazy two minutes before she made sure every last drop was squeezed dry. Then she rested her head on my chest.
I stare blankly at the roof of the bunk bed, trying to process my rape. I don’t know what to feel. It was humiliating, painful and enjoyable. Stef then looks up at me.
“From now on, you are under me. Anyone bully you, just say my name.” she said.
I looked away, refusing to acknowledge my beautiful rapist. She lets out a giggle, petted my head, then finally got off my cock and help me pull up my pants. How many more times is she going to rape me while I’m in here? If I complain to the guards, will they put me in solitary confinement, or worse, with another sex starved cellmate who might be even more violent? As I processed my thoughts, she grabbed me and wrapped her arms around me, resting my head on her breasts, hugging me like a bolster. I really felt like punching her but I’m too tired now and just napped in her arms.
Massive thanks to all bros for support and compliments!
-——————————————————————————-
Stef woke me up as it was time to go out for dinner. She held my hand and protected me as she promised as we made our way to the canteen, and everyone stared at me like they wanted to eat me. I had no choice but to stick closer to her. As we all queued up to get our food, I got molested multiple times when the girls behind me grabbed my ass and my crotch. I complained to Stef who was in front of me, and she quickly switched spots with me while giving the other girls a death stare.
As we got to our table to eat, the guard in charge, Mdm Ying, approached me.
“Hey newbie. Everything ok in here so far?”
Stef didn’t even bother to turn. She knew I wasn’t going to tell that she had raped me just now.
“Yes ma’am, thanks for asking. Everything is fine.”
She picks up my arm.
“How come you have a bruise on your arm? Did anyone bully you?”
“No ma’am, I…knocked on the cell door. Really, I’m doing ok.”
“Later come first aid room and see me, I help you put some ointment. You all better don’t bully him understand?”
Everyone at the table complied with a “yes madam”. I felt touched…finally someone who showed me real concern in here. But Stef quickly leaned in, grabbed my balls and warned.
“You better don’t tell her any nonsense or tonight you will get it, understand? If they transfer you to a different cell, I make sure whoever’s with you will abuse you worse than I!”
“Ow ow…yes zehzeh!”
She let go, smiled, and then gave me her chicken drumstick. This sick woman is abusing and warming up to me at the same time, I dunno how I’m supposed to feel about her.
After dinner, I head to the medic room to see Mdm Ying for medical attention. She’s very cute, especially when she smiles. The blinds are drawn as she grabbed a tube of ointment and began applying it on my forearm on the spot where Stef had bruised me in my struggle against her rape. But as she lifted my sleeve, she saw another bruise.
“2049! What is this?”
“Nothing madam!”
“You say you knock on cell door how many times?”
I stayed silent.
“If you don’t tell me how am I supposed to help you? Were you raped?”
My eyes widened at the word, but I quickly remained my composure and kept my lips sealed. Mdm Ying puts her hand on her face, frustrated that I refused to eat out my abuser.
“Stand up and take off everything.”
I’m unwilling, but did as she told and stripped naked. Thankfully, there weren’t many other injuries, but my cock was still sore and she could see it. There are also a few bruises around my groin area from Stef’s rough riding. Mdm Ying put on latex gloves, applied a cool gel on her hands, and then started stroking my penis. The coolness stings at first, but slowly became pleasurable and subdued the pain. Her other hand moved to massage my balls.
From this angle, I was able to stare inside Mdm Ying’s uniform and see that she’s wearing a lacy light pink bra. Her breasts are quite ample too. My cock inevitable started getting hard from this combined stimulus. Mdm Ying looks up and noticed what I’m looking at.
“You looking inside my shirt?”
“Sorry madam! Accidentally!”
She treated it as nothing and continued stroking me, even as my cock got harder and harder. Her face was also really close to my cock, that I could feel her warm breaths landing on my penis. Precum was leaking out and getting all over her hands, but she couldn’t tell because of the gel. She stroked and groped and I continued staring at her bra…until I finally buay tahan.
I ejaculate, and the first line of semen struck her on her lips, the second on her uniform, and the rest all over her pants. She quickly takes a step back to dodge, but most of the damage had been done.
“Bloody hell! Who said you can cum! Want to cum also never make noise!” she yelled angrily while spitting out the cum that got on her mouth.
“Sorry ma’am sorry!!” I apologised profusely even as I was still ejaculating the last of my sperm.
Mdm Ying was quite forgiving and just silently wiped everything with tissue paper. She must be feeling sorry for me being abused in here. Still, I felt damn bad that this nice prison officer had been trying to help me, and yet I came all over her.
“Go shower!” she ordered.
“Yes madam! So sorry again!”
I put my clothes back on and headed to the shower. Stef isn’t around to protect me, but seeing that it was empty, I stripped and finally got some alone time to gather my thoughts. I keep weighing my options on whether or not I should report Stef to the guards…could it mean more trouble for me? The prison is small and she will always be able to take revenge on me.
Just then, to my shock, I hear a number of footsteps enter the shower. I had thought about dashing off, but who knows, maybe they mean me no harm. And showing them that I’m scared may embolden them to bully me more. I decide to stay calm and play it cool.
There were altogether six of them, and three took up the spots to my left, three to my right. I try my hardest not to look at them yet appear natural, but my body language is betraying me…I’m clearly nervous. Then, the one on my right started talking to me.
“Hey boy boy. Nice cock.”
They all laughed and I pretended not to hear. I started rubbing my body with the bar of soap in my hand when the lady on my left suddenly slapped my ass, causing me to drop the soap.
“Oi! Stop bothering me!” I yelled. They have crossed the line.
“Ok ok. Bend down and pick up the soap. Then we won’t bother you.”
All six started to form a circle around me. I’m not getting away with this one. I gave them a cold hard stare, as I very, very slowly, bend down and reach for the soap…
“OWWW!!!”
I felt a finger go up my ass and it fucking hurt! It went deeper than when ASP Leow searched me! Then another hand grabbed my balls hard, causing me to wince and scream in pain. I start resisting, swinging my arms wildly to fend them off, but I’m no match for them one on one, never mind all six. Very quickly, I am pinned down, with four of them holding down my arms and legs, and one of them grabbing me from behind, putting my neck in an arm lock and grabbing my hair with her free hand to face the remaining one, presumably the leader.
“Let me go! I am under Stef! She will not let you off if you touch me!” I roared as I struggle with all my might fruitlessly. They were so strong.
“Stupid boy boy. Your zehzeh told us to have our way with you here - it’s to settle her gambling debt from last week. Look at your delicious cock…limbu hungry already!”
She gobbled down on my cock and I tried to scream for help, but the girl holding me from behind changed her arm lock into covering my mouth. I could feel the rough suction on my cock forcing me to get aroused again, against my will. She kept poking her finger in my ass as she sucked me off.
Then she got on top of me, and rode me. I could only make mm mm sounds as she brutally raped me in the shower. It didn’t matter than she’s actually quite attractive - she fucking me against my will. I stared at the ceiling as every second felt like a minute, and after when felt like forever, I finally cum inside her pussy.
But of course, it wasn’t over. My assailant high fives and switched places with the girl holding down my left leg, like it was WWE tag team, and she did the same thing…blowing my cock up and then riding and raping me. With each rape it took longer for me to cum, but they would squeeze my balls to force semen out of me, and it took nearly an hour for all six of them to finish gangraping me.
Brutally gangraped by women
Finally, it was over. I lie down in a fetal position as my cock and balls are sore as can be. They joke among themselves on how shiok my cock was and that I was a better dinner than what they served at the canteen, just to humiliate me more. As they leave the shower, someone comes in to help me up. It’s Stef.
I really want to kill her. This bitch with all her bullshit about protecting me, in the end I kena gangraped thanks to her. She tried to help me up but I refuse to get up.
“Sorry lah, I know zehzeh let you down. They were definitely going to rape you at some point, but this way you also get to clear my gambling debt. I go back treat you eat biscuit ok?”
I’m still unmoved.
“Oi! I apologise already you still wanna attitude? Soft style cannot you want me to use hard style?”
Fuck. I didn’t have a choice. I slowly got up as she helped me put my clothes on, and limped out of the shower with her holding my arm. I could barely walk…my balls felt like burning with every step I take. Whenever we run into a guard, Stef would just tell them I’m having muscle cramps.
We got back to our cell, and it’s finally lights out. Stef wrapped her arms around me and slept like a log, but I remain awake. First day in prison already kena gangrape. And I’m sleeping in the arms of another person who raped me.
Fuck it, I’m telling ASP Leow.
The next morning, I approached Mdm Ying to make a request to see ASP Leow. She’s very concerned for me, and managed to help me make an appointment in the afternoon. I managed to stay out of harm for that period as Stef knows I’m still sore from last night, but she couldn’t resist groping and molesting me every now and then.
I am escorted to ASP Leow’s office and Ying takes her leave, leaving me alone with Mdm Leow who sits behind her desk. I’m surprised at how well equipped it is. Half of it is a typical office with a desk, chair and file cabinets, but the other half is essentially a bedroom with a queen sized bed and even a bathroom attached…amenities privy only to the higher ups.
“Have a seat.” she said. But I couldn’t…my balls are still sore.
“It’s ok ma’am, I prefer to stand.”
“So why did you want to see me?”
The answer to that is so heavy, but I am not keen on beating around the bush either. I get flashbacks of what happened in the bathroom, which provoked me to spill out everything.
“I was gangraped in the shower yesterday, ma’am. Six women took turns to have their way with me. My cellmate Stefanie also raped me before that.”
I could only look down after saying that. It felt so bad having to say those words.
“Are you sure? That is a very serious accusation, 2049!” she barked.
“I swear madam! On my life!”
“Aiya…strip naked, let me check!”
Not again. Even though I have bared my body to ASP Leow before, it doesn’t get any more comfortable this second time. She watches intently as I removed my clothes bit by bit, and was soon completely naked. She gets off from her chair and uses her hand to roam on my body again, just like yesterday’s search, but with no gloves this time. She lightly pressed my chest.
“Here pain?”
“A bit, ma’am.”
Onto my abdomen.
“Here?”
“Quite painful, ma’am…”
She reaches down and gives my cock head a light pinch.
“OWWW!!!” I yelled.
“Poor thing. I help you apply some ointment.”
She reached into her drawer and took out a small bottle, put a bit of that gel like substance on her hand, and started applying it to my genitals. It was painful at first but this ointment is of an ever higher grade than the one in the medic room, so it relieved my sore even quicker, although there’s still a lingering pain.
“Thank you madam. So can you help me…I don’t want to everyday kena rape.”
“Prison is like that one. You should have never committed a crime in the first place. Unless you have a high ranking prison guard to back you, otherwise they will keep on raping you.”
“Ma’am…are you talking about yourself? Will you back me?” I asked pleadingly.
She’s silent for a while, before letting out a sly grin and grabbing my asscheek.
“It depends on how good a boy you are.”
FUCK. Even ASP Leow wouldn’t let me off. I have started to develop a phobia for sex at this point, but I must tahan whatever she demands if I’m going to have any peace.
“I…will be a good boy, ma’am.”
“Use mouth say who dunno? Must use actions.”
She hikes up her skirt and pulls down her panties. Then she sits on the desk and spread her legs wide, showing off her well shaven cunt to me.
“Use your tongue.” she said.
I can see the pussy juices already leaving from her vagina, she must have wanted to get intimate with me the moment I walked in. I kneel down reluctantly, slowly sticking out my tongue…and sink it in the hole between her legs.
I licked diligently and sank my tongue inside her pussy as deep as I can to please her. She’s moaning louder and louder, and even used her legs to lock me and press my head against her below. As I continued to stimulate her, I can feel her squirting on my tongue. I tried to spit out but she pressed me so close that I had no choice but to drink her squirt.
“Very nice, little boy. Time for me to play you.” she said, as she opened up a closet which had all sorts of nasty bdsm toys.
No mercy from Mdm Leow
“No…no! I did as you asked! Let me off!” I begged, as I run towards the door trying to escape. But she quickly grabbed me and I was no match for her strength. She cuffed my hands behind my back, my legs together, then blindfolded me and put a ball gag in my mouth, before tossing me onto the bed. To prevent me from hopping away, she put a collar on me and tied the leash to the bed frame. Here I am, naked, cuffed up and helpless, at her mercy. I continue to make fruitless struggles.
“被我脱光衣服捆在这里，根本跑不掉，你还不认命?” she said, suddenly returning to her more comfortable native tongue about how helpless I am. She speaks like a channel 8 actress. I continue to fight against the cuffs to no avail. She put another pair of cuffs to lock the mid section of my leg cuffs to the bedframe, and I am now forced to lie flat, with my collar pulled to the other end. I can feel her tongue going from my shin to my thighs, then onto my balls and cock. She continues her tongue journey across my torso and arms, to my cheeks, until I was covered in her saliva. Then she whispered to my ear.
“Let madam show you what is real rape.”
“MMMMM!!! MMMHHMMM!!!”
I tried to beg her for mercy but those were the only sounds I could make. She ignores me and sits on my cock HARD, and rode me rougher than the others ever have. She would also pinch me in various places repeatedly and also told me she’s taking a video of my struggling, often goading me to “struggle more, like that watch liao more shiok.” She rode me for a intense fifteen minutes and ordered me to cum. I shook my head in defiance, but I still came anyway, my cock completely at her mercy, as I ejaculated deep inside ASP Leow. Although it is my organ lying in her, but her dominance and conquer over me is undisputed.
Optional ending for this chapter: The following contains dildo ass rape, so you may enjoy or skip according to your tastes!
( Click to show/hide )
Her next words would scar me forever.
“You’ve fucked me. Now time for me to fuck you.”
She turned me to lie on my belly and opened up my leg cuffs, only to spread them apart and cuff them to the bed edges. I could hear the sound of a vibrating dildo and the squeezing of a tube of lube, feeling a cold gel being applied on my anus. Then the sound of harness being strapped on. Fuck fuck no!
“You ready?” she teased as she aimed the tip of her strap on rubber cock on my asshole. I make one last insane struggle and yelled as loud as I can to deter her.
“MMMMMMMHHHHMMMM-”
In the middle of my loud moan, she thrusted four inches of dildo on her strap on inside my ass. The lube almost didn’t help at all. She trusted and thrusted and picked up speed as she sodomised me while grabbing my hair like a rapist would. I felt my prostate being pounded as I approach a first in my life - a prostate orgasm.
“You make Madam shiok. madam also make you shiok! Madam make you cum non stop!!!” she said as she continued to fuck me.
I let out a loud moan and clutched my hands and feet as I had a prostate orgasm. It’s ridiculously intense, yet because there’s no ejaculation, there’s no cooldown period either. She toyed with my prostate as I came over and over and over again. After an uncountable number of orgasms, I finally pass out from rape.
I wake up on the bed, the restraints all gone but still fully nude, with her arms around me like a beast with her prize. I tried to feel up my butthole and it is sore like mad. Mdm Leow cosy up to me and whisper “No one will touch you for a while, I promise you. You were a good boy. A good whore boy.”
I stare blankly into space. I swear I will take revenge on this bitch who raped my ass.
ASP Leow refused to give me any pain reliever for my new bruises, insisting she wants me to remember her through the pain, and that our next session is not far away. She warned me that I have no proof against her and will be thrown in solitary confinement if I run my mouth off. I could only limp to Mdm Ying and ask her for help again in the medic room, but she would not accept me if I refused to talk, and instead referred me to Dr Liu. Dr Liu is not only a physical physician but a psychiatrist as well, and Ying hoped that she would give me the courage to finger who raped me.
Dr Liu is caring, unconventional but also great at her job
I headed over to see Dr Liu and she seemed very concerned about me. I could tell from her eyes - she had been working here long enough, one look can tell I had kena raped, and not just once. She just went ahead with her questions.
“Tell me where it hurts.”
I pointed to my cock shyly, and she very willingly helped me to remove my pants, exposing my genitals for her to see. She did not even wear gloves as I felt her caring touch on my cock, thankful that there’s someone else other than Mdm Ying who seemed concerned for me. She slowly applied a cool gel on my penis, then my balls, and then sank her fingers very delicately inside my anus. I winced a little and she patted my thighs to calm me down.
“It’s ok, it’s ok, Dr Liu won’t hurt you one.”
After the application, she wrapped a towel around my waist and led me to a sofa. She rested my head on her lap and started trying to coax me to say what happened. Her thighs are soft and warm, and I wish I could lay here forever instead of going back to the prison bed. My head is facing towards her, and her short skirt crawled up in sitting position, allowing me to see her satin panties. I could even smell the sweat from beneath her, as I’m starting to get aroused again.
“Joe, I is in charge of the well being of all inmates in this prison. I want you to know that it’s ok to tell me everything. The guards will protect you.”
Those words had the opposite effect…it is precisely the guards I’m afraid of. Other than ASP Leow, who knows which other guard have set their sights on devouring me. I continued to keep my lips sealed. But my hard on is getting stronger, and she soon noticed.
“Joe, you having dirty thoughts about me?”
“No, no! Sorry Dr Liu, I just…it’s nothing.”
To my surprise, she raised her skirt all the way, revealing her panties fully.
“Dr Liu! What are you doing?”
“Fostering trust and love with my patients is what I do. I want you to know that in this room, I am your doctor, your friend and your lover. I want you to pour your heart out to me, can you do that?”
I’m stunned and have no clue how to reply. Seeing this, she took off her coat, and began removing her shirt.
“Dr Liu, stop! You shouldn’t degrade yourself like that!” I pleaded.
“There’s nothing degrading about this. I have already seen your penis, it’s only fair that you see my private parts as well.”
Thanks guys, but bro Rickey’s comment inspired me to make a spinoff haha, will put this story on hold first
Quote:
Originally Posted by
Rickey
Damn sexciting fantasy story..
..how we wish the female doctors conducting medical check-ups on us, says this to us
..hehe